Water → Piperidine, 4-(diphenylmethylene)-1-methyl-

HRID 458003

Reaction equation

HRID 458003 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(O)[CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.O>C(Cl)Cl>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2014851-Methyl-alpha,alpha-diphenyl-4-piperidinemethanol

Product 1

HCID 95734Piperidine, 4-(diphenylmethylene)-1-methyl-Yield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Compound 9 (2.0 g, 6.41 mmol., 1.0 eq.), K2CO3 (1.77 g, 12.82 mmol., 2.0 eq.), halide (5.28 g, 32.05 mmol., 5.0 eq.) and DMF (25.0 mL) were combined and heated to 100° C. overnight. The crude reaction mixture was mixed with H2O (30 mL) and CH2Cl2 (35 mL). The organic phase was separated and the aqueous phase was washed with CH2Cl2 (2×25 mL). The combined organic phase was washed with brine and concentrated. The crude material was purified on a silica column to give compound 10 (1.2 g). The structure was confirmed by 1H NMR and LC/MS.

Workup

  1. customThe crude reaction mixture
  2. customThe organic phase was separated
  3. washthe aqueous phase was washed with CH2Cl2 (2×25 mL)
  4. washThe combined organic phase was washed with brine
  5. concentrationconcentrated
  6. customThe crude material was purified on a silica column

Sources & evidence

ORD record
ord-22d553c62e714635bf51c1c4b28f0fc7
Source dataset
uspto-grants-2007_03
Patent number
US07189757B2

Linked notes

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